Synthesis of amino-substituted pyridylglyoxylamides via palladium-catalysed aminocarbonylation

Palladium-catalysed aminocarbonylation of iodopyridine model compounds (4-amino-3-iodopyridine and 3-amino-4-iodopyridine) with various primary and secondary amines including amino acid methyl esters was carried out. The two substrates behave in a completely different manner under aminocarbonylation conditions: 4-amino-3-iodopyridine gave the corresponding 2-ketocarboxamides (nicotinamide analogues) due to double carbon monoxide insertion, while 3-amino-4-iodopyridine reacted as a bifunctional substrate resulting in a dicarboxamide containing two pyridyl moieties.